Synthesis and screening of ( E )-1-(β- d -galactopyranosyl)-4-(aryl)but-3-ene-2-one against Mycobacterium tuberculosis

C-Glycosylated cinnamoylfuran derivatives as novel anti-cancer agents

“…Aer a set of optimizations, it was found that the use of 1.0 equiv. of sodium methoxide furnished an excellent yield (75%) of the desired product (7) in 12 h. Therefore, compound 4 was allowed to condense with a series of aromatic aldehydes in the presence of sodium methoxide in methanol to give C-glycosylated cinnamoyl furan derivatives (7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20)(21)(22)(23)(24) in excellent yield. The formation of the trans-cinnamoyl double bonds (E-isomers) in the molecules was conrmed from a 1 H NMR spectral analysis [doublets with large coupling constant (J ¼ 15.5-16.0 Hz)].…”

“…8,9 In the recent past, C-glycosylated heterocycles, such as C-glycosylfuran derivatives and related compounds, have been reported for their therapeutic potential. [10][11][12][13][14][15] In addition, a variety of cinnamoylated C-glycoside derivatives have been synthesized with a similar sugar moiety but different aryl groups and evaluated for their potential as anti-mycobacterial agents, 16,17 anti-cancer agents, 18 lectin inhibitors, 19,20 enzyme inhibitors, 21 and anti-larial agents. 22 Inspired by these earlier reports, it was decided to synthesize a series of C-glycosylated cinnamoylfuran derivatives to evaluate their potential against cancer cell lines to develop novel anticancer agents.…”

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2011–2012

“…Synthesis of a universal fluorescent acceptor for HPLC analysis of pro-and eukaryotic polysialyltransferases (Keys et al, 2012) Endohedral metallofullerene glycoconjugates TOF Synthesis by carbine addition Fluorous-tagged glycosides TOF Incorporation into cell membranes (Hatanaka, 2012) O--D-Galactopyranosides TOF/TOF Synthesis and preliminary screening as potential mimic of UDP-Galp against Mycobacterium tuberculosis (Mugunthan et al, 2012) Galactose-appended naphthalimide TOF For intracellular hepatocyte thiol imaging in vivo Galactose-derived aryl enones TOF Synthesis and screening against Mycobacterium tuberculosis (Mugunthan et al, 2011c) Glyco-functionalized platinum complexes TOF (DHB), FAB Functionalized with malonate for complexation with Pt for cancer treatment 2012) Glycoporphyrins Q-TOF Synthesis and biological evaluation (Daly et al, 2012) Glycosyl carbamates TOF Use of propargyl 1,2-orthoesters as glycosyl donors Lactose-PEG neoglycolipids TOF (2,4-DHB) Synthesis and mutagenicity properties (Dmochowska et al, 2011) Saccharide-functionalized alkanethiols…”

5-Hydroxymethylfurfural (HMF) in Organic Synthesis: A Review of its Recent Applications Towards Fine Chemicals

“…A condensation with 1-C-(-D-galactopyranosyl)-propan-2-one in the presence of lithium hydroxide was performed to prepare galactose derivative 12 in 65% yield, which proved to be an effective antimycobacterial agent (Scheme 5). [33] A C-4 epimer of 12 could also be prepared from 1-C-glucosylacetone in dichloromethane in the presence of pyrrolidine in 87% yield. [34] Scheme 5.…”